1: 82 percent / Raney Ni / ethanol / 1 h / 0 °C 2: 95 percent / Dess-Martin reagent / CH2Cl2 / 1 h / 23 °C 3: tetrahydrofuran / 0.5 h / -40 °C 4: NH4Cl, H2O / tetrahydrofuran / 0.5 h 5: 99 percent / H2 / Pd/C / ethanol / 12 h / 23 °C 6: 87 percent / TFA, H2O / 4 h / 50 °C 7: LiOH, H2O / tetrahydrofuran / 0.5 h / 23 °C 8: bis(2-oxo-3-oxazolidinyl)phosphinic chloride, Et3N / CH2Cl2 / 0.5 h / 23 °C 9: 62 percent / ceric ammonium nitrate, H2O / acetonitrile / 1 h / 23 °C View Scheme